Polyvinyl chloride plasticized with a chloroalkylchlorobenzene compound



Patented Oct. 28, 1952 POLYVINYL CHLORIDE PLASTICIZED WITH A CHLOROALKYLCHLOROBENZENE COM- POUND Andr Gislon, Paris, France, assignor to Compagnie Francaise de Rafiinage (Societe Anonyme) Paris, France No Drawing. Application March 7, 1947, Serial No. 733,189. In France February 20, 1946 Section 1, Public Law 690, August s, 1946 Patent expires February 20, 1966 3 Claims. 1

I have found that aromatic components substituted by aliphatic and halogenated chains on the nucleus and/or on the side chain or chains form valuable plasticizers chiefly adapted for use in the treatment of polyvinyl chlorides.

Hereinafter are given two examples of the manner in which such compounds may be prepared, it being understood that the present invention is not limited to the details set forth in these examples.

Example .1

A gas oil of aliphatic nature, chlorinated at 30%, is condensed with benzene by any usual method. In addition to viscous products adapted to be used as lubricants, the condensation reaction produces as by-products aromatic com- Example 2 An excess of monochlorobenzene is condensed in presence of aluminum chloride with a fraction of Fischers gas oil the boiling point of which under a pressure of mm. of mercury ranges from 80 to 167 C., said oil having a mean molecular weight equal to 225 and being chlorinated at (the excess of chlorobenzene corresponding to about 12 moles of said product in the mixture as against one mole of chlorinated gas oil). After condensation, which results in the removal of all of the chlorine bound vto the aliphatic hydrocarbon chain, the sludges are separated from the aluminum compound after which the product is washed with water and the excess of monochlorobenzene is distilled off.

The compound obtained is then rectified in vacuo and the fraction the boiling point of which under a pressure of 20 mm. of mercury ranges from 200 to 250 C. is then overchlorinated in presence or not of a diluting medium and in the absence of any catalyst until it shows a total content of 38% of chlorine.

The chloroalkylchlorobenzene thus prepared may be used as a plasticizer either as itis or after rectification.

2 It has been compared with tricresylphosphate in three operations ABC, the results of which are shown in the following table.

A B O Polyvinyl chloride, percent 60 60 Tricresylphosphate, percent 40 0 20 Oliloroelkylchlorobenzene, percent 0 40 20 Tensile strength, kg./mn1. 0.88 1.28 1. 26 Elongation, percent 269 300 310 Shore hardness at 25 C 73 78 S0 Shore hardness at 80 C 56 55 r 55 What I claim is:

1. A plasticized'product comprising a vinyl chloride polymer and a plasticizer which is a chloralkylchlorobenzene compound, said com.- pound being made by condensing aliphatic gas oil which contains about 30% chlorine with a compound selected from the group consisting of benzene and monochlorobenzene and thereupon chlorinating the resulting condensation product to about 40% chlorine content.

2. A plasticized product comprising a vinyl chloride polymer and a plasticizer which is a chloralkylchlorobenzene compound, said compound being made by condensing aliphatic gas oil which contains about 30% chlorine with benzene and thereupon chlorinating the resulting condensation product to about 40% chlorine content.

3. A plasticized product comprising a vinyl chloride polymer and a plasticizer which is a chloralkylchlorobenzene compound, said compound being made by: (a) chlorinating to about 30% chlorine content a fraction of Fischer gas oil, said fraction having a boiling range of between about 80 and 167 C. at 25 mm. Hg pressure and also having an average molecular weight of substantially 225; (b) condensing said.

chlorinated fraction of Fischer gas oil with monochlorobenzene and; (c) chlorinating the resulting condensation product to about 40% chlorine content to yield said compound.

ANDRE GISLQN.

REFERENCES CITED The following references are of record in the file of this patent:

UNITED STATES PATENTS 

1. A PLASTICIZED PRODUCT COMPRISING A VINYL CHLORIDE POLYMER AND A PLASTICIZER WHICH IS A CHLORALKYLCHLOROBENZE COMPOUND, SAID COMPOUND BEING MADE BY CONDENSING ALIPHATIC GAS OIL WHICH CONTAINS ABOUT 30% CHLORINE WITH A COMPOUND SELECTED FROM THE GROUP CONSISTING OF BENZENE AND MONOCHLOROBENZENE AND THEREUPON CHLORINATING THE RESULTING CONDENSATION PRODUCT TO ABOUT 40% CHLORINE CONTENT. 